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“Did you bring your riding gear?”

Jimmy Day, slumped against the rain, water dripping off the salt and pepper stubble on his chin, navy rain coat and pants long defeated, looked up from the back of allowance winner Our Emerald Forest (Ire) and asked that simple, yearning question. With one set still to go, Day was looking for reinforcements.

It was that kind of morning at Daybreak Farm–cold, wet, dark and a long way from any winner’s circle. Day’s wife, Emily, had given her foxhunters the day off, but the racehorses needed to train. This is when races are won, in the long, slow, trudging days of February. Most of the snow from Winter Storm Jonas had melted–but the rain had come, soaking Day, his two riders and everything across the 123-acre farm in White Post, Va., 23 miles northwest of Middleburg and 23 miles southwest of Charles Town.

But, don’t be fooled by the desultory scene. This is where Day does his best work, far from the spotlight.

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A year earlier, through days just like this, the Irish-born trainer readied Diplomat for his American debut in the Carolina Cup, the first big novice stakes of the 2015 steeplechase season. The son of Kitten’s Joy trounced fitter southern-based runners. That’s not supposed to happen. A few months later, in the stifling heat of a Vir­ginia summer, this is where Day primed Diplomat, Plated and Bonded (Ire) to win over hurdles at Saratoga, contributing to Day’s most lucrative season since he began training in 1988.

Last year, he won eight jump races and four flat races, his horses earning $448,496. The numbers don’t sound big, but it’s not about the numbers.

Jumpers and flat horses, ranging from homebreds to imports, and pinhook prospects make up the Days’ game plan. Yearlings by Drosselmeyer and Bluegrass Cat, 22-year-old Flasher, second in the Riggs on the flat and a winner of the Joe Aitcheson Stakes over jumps, and retired broodmare Dancing Ballade make up the population on the farm. It’s hard to make a living training jumpers in America, Jimmy and Emily know it, accept it and try to create other ways to make it in the horse business, mostly by breeding a few each year, owning a couple when the timing’s right and/or pinhooking some 2-year-olds every year.

“We keep a lot of pots on boil,” Emily said. “Our horses have to be good at a lot of things.”

In the realm of racing success, perhaps, Jimmy and Emily Day have hit the biggest home runs from the shortest and farthest distance.

They sold eventual Grade 1 stakes winner Mandy’s Gold for $87,000 at the Fasig-Tipton Midlantic 2-year-old sale in 2000. Day bought the Audley Farm-bred daughter of Gilded Time privately and prepped her for the sale, handing her to consignor Eddie Woods when he arrived at Timonium. Six years later at the same sale, the Days sold a homebred son of Holy Bull out of Dancing Ballade for $410,000. Consigned by Woods, Like a Bull was bred, raised, broken and prepped by Day. The Days have won the Carolina Cup four times, the New York Turf Writers Cup, the A.P. Smithwick and other steeplechase stakes going 2 miles and farther. All achieved “over the mountain” in Clarke County, far off the beaten path of a 1-mile dirt oval or an established training center.

“I couldn’t do it at the racetrack, I’d rather lay blocks, the track is a tough life. There are no breaks, it’s not a healthy way to live,” Jimmy said. “We had dinner with Graham [Motion], he is under pressure. It comes back to one person, the buck stops with one person.”

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Along the way, the Days raised two children, Ian and William. They graduated from William & Mary and have embarked on real lives away from baling hay and walking horses on the family farm. Ian is in law school at William & Mary and engaged. William lives in the Adams Morgan neighborhood of Washington, D.C. He sold his car and takes the metro to his job as a data analyst at GEICO.

“They’re flapping their little wings. It’s fun to see them independent and happy, living their lives confidently,” Emily said. “They know what they’re doing with horses but they just chose not to do it. Our kids were like ‘That looks like a lot of work for a lot of heartache.’?”

If you look back at the day when Jimmy and Emily got married in 1989 well, they wouldn’t have been the favorites of their generation to survive, much less flourish. Jimmy, one of 11 children from County Wexford, Ireland, had finished off a modest riding career and was thinking about becoming a trainer, without backing or ancestry in the game. Emily, daughter of prominent veterinarian and editor Dr. Matthew Mackay-Smith and his wife Winkie, was on her way to a psychology degree at the University of Virginia when she dropped out, three semesters short, to marry Jimmy (she went back and graduated a few years ago).

“My parents totally freaked out,” Emily said. “In the way that they would, not like, ‘You can’t do that!’ Just, like, ‘She’s making a grave error.’ They didn’t think it was a good idea.”

No, these two didn’t have a shot.

But then they did.

“It’s a commitment,” Emily said. “It’s hard sometimes, you’ve got to get over yourself and get along, most people don’t want to.”

“That’s exactly what it is, it’s a commitment,” Jimmy said. “I think most people take it too lightly.”

They met in 1986, at a Christmas party at Joy Valentine’s farm in Unionville, Pa. Valentine threw the party for Hall of Fame trainer Burley Cocks, who had won his final training championship that year. Jimmy, who came to America in 1983, galloped and rode as third-call jockey for Cocks–his claim to fame might have been the way he handled the enigmatic Turtle Head in the mornings. After the party, Jimmy tracked down Emily in Ireland–they had gone there separately on vacation–and then tracked her down again in May and invited her to the Fair Hill Races. Emily was working for Ami Shinitzki, a polo player and editor of Equus Magazine, in Potomac and said she couldn’t go because she worked on the weekends. Jimmy had an answer, the Fair Hill Races were on Memorial Day Monday. She drove a beat-up car with a cracked piston to the races, watched Jimmy win a maiden claimer on future Maryland Hunt Cup winner Von Csadek (he was the only one in the jocks’ room who would ride him), fall on Heated Talk, finish last on Fools Art and finish sixth on Once More Twice. And the rest is history.

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Always interested in breeding horses, but without the capital to properly engage in that sphere, Day turned to training. In his first year, he won three jump races with the over-achieving Limaton (Chi). A year later, Day won flat races and jump races with Irish import Intelligent Choice (GB). The ball was rolling. He rented some stalls at Arthur Choate’s farm adjacent to the Pennsylvania Hunt Cup course in Unionville, before renting a few stalls from George Strawbridge Jr. in Andrew’s Bridge, Pa. Fledgling, Day got a call from Michael Motion (father of Graham and Andrew) about moving to Audley Farm in Berryville, Va.

It was an easy decision. Jimmy managed Audley’s horses and trained his own from the historic farm where Triple Crown winner Sir Barton stood as a stallion. It worked perfectly. When that dynamic changed, Jimmy and Emily moved their horses to Martha Cook’s Claytonville Farm in Millwood, Va. She owned horses, including hard-knocking Joli’s Summer and Carolina Cup winner Canta Ke Brave, the Days stayed at Cook’s until she died in 2007, then made their final move to part of Emily’s parents’ farm, just down the road from the white post in White Post.

Sitting in Jimmy and Emily’s open-air kitchen in the house Like a Bull built, it’s easy to see why they’re still going strong.

They correct each other, consistently, but without edge, scoreless, barely noticing. They complement each other, Jimmy knowing the horses, Emily knowing the details.

Jimmy tells a story about trying to buy a farm in Pennsylvania.

“Don’t put that in,” Emily says.

“I don’t care what you put in there,” Jimmy says.

Jimmy tells a story about a crazy filly who jumped a metal gate.

“Jimmy, why don’t you tell him stuff he wants to put in the article?” Emily suggests.

“This is fact,” Jimmy says.

This goes on through the whole lunch?–homemade chicken salad and soup whipped up and served by Emily.

“We bought Like a Bull’s mother, Dancing Ballade, as a yearling from Rick and Dixie Abbott,” Emily says. “We borrowed $30,000 to buy her.”

“How much?” Jimmy asks.

“Thirty grand.” Emily says.

“Thirty-four,” Jimmy says.

She cost $31,000.

And changed everything.

Purchased as a yearling from Adele Paxson through the Abbott consignment in 2000, the full-sister to Pennsylvania Derby winner Devil’s Honor made four winless starts on the flat in 2001. Bred to Holy Bull, she gave birth to a robust colt. Consigned to Fasig-Tipton Kentucky as a yearling, he failed to sell for $47,000. Jimmy brought him home to the farm, at Claytonville, and began to prep him for the 2-year-old sales.

OK, imagine the typical 2-year-old consignor in Ocala–big sets, big belt buckles, whips in the back pockets, stop watches beeping, accelerating at the pole, blazing furlongs on a dirt oval. Now erase it.

“We do it a little differently, for sure,” Emily said. “As Jimmy says, ‘Look, if they’re fit and they know how to sprint, let them do their thing.’ ”

Jimmy jogs his babies a half-mile, canters a quarter-mile, and lets them rip 100 yards uphill, twice a week. He takes them to Charles Town to get used to a track, the action. He never lets them get tired, they never get shins and they turn up at Eddie Woods’ consignment the day before the money breeze. Then run a hole in the wind.

“His horses come in sitting on go, they’ve come in ready for years. We usually have nice horses because he buys a nice horse. He tells you how far they need to go, they come in and gallop two rounds of Timonium and away they go,” Woods said. “The guys who came up as kids through the jump circuit, they have an edge. It’s a feeling of knowing that [stuff] is going to go wrong, you catch it before it goes wrong. Jimmy’s got that.”

Mandy’s Gold, a private purchase from Audley, worked fast, fetched $87,000 and became a Grade 1 stakes winner. She built two run-in sheds and seeded two paddocks at Daybreak. That was a score.

Dancing Ballade’s first foal, well, that was a different stratosphere. Two weeks after Holy Bull’s son Giacomo won the Kentucky Derby-G1, Woods called Day Sunday night, the night before the sale, and told him there was real money on him. Day was getting on the ferry, lashing rain, on the way home from Potomac Point-to-Point.

Running horses for no money and thinking about big money, the Days relish in the memory.

“That was the most nerve-wracking, adrenaline filled moment of my horse life,” Emily said. ‘My heart was pounding. It was amazing, surreal, like an out-of-body experience. He built the farm, literally.”

Again, Jimmy echoed Emily’s sentiments.

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“He built the place,” Jimmy said, as he drove his four-wheel drive pickup with a shotgun in the front and a round bale of hay in the back around the farm. He started at the center-aisle barn, pointed out the rolling gallop in the front, past paddocks, around the field where the timber horses live, past Emily’s parents’ house, to Flasher and Dancing Ballade’s field, past recuperating hurdler Cul Baire (Ire) and an unraced 2-year-old, along the woods and to the edge of his pride and joy–a 70-foot wide grass gallop that extends a mile, straight.

“See, the round-topped tree?” Emily said. “That’s halfway.

Not exactly 11-second furlongs measured here.

The fifth and last stop on their migratory career as horse owners and trainers, this is home.

As Jimmy slipped the truck in and out of four-wheel drive on the fly–and Emily tried to cajole him not to–the farm’s story came to life. Part of the Mackay-Smith’s farm, in Blue Ridge Hunt country, it was nothing but corn when they started.

“That’s how we got the land, I don’t underestimate that in any way, it’s been a huge gift to us, but it didn’t come with a trust fund, every single penny we’ve spent to turn a corn field into this has been made from us working in the horse industry,” Emily said. “There aren’t a whole lot of people who pay all their bills by training horses, as my father said a long time ago, it’s a lot easier to do horses with money than for money.”

Mindful but undaunted, Jimmy and Emily continue to produce winners, either in the sales ring or on the racecourse.

Day has won 204 races from 2,023 starts since 1991. Daybreak has won 36 races from 266 starts and $841,899 since 2000. They’re not afraid to be owners, sending horses to Dove Houghton, Ollie Figgins and other flat trainers along the way. The eclecticism of their endeavor is showcased upstairs in their high-ceilinged office. Win photos range from Jimmy on splay-legged jumper Bold Mac Crackpot at Callaway Gardens in 1986 to Jacinto Vasquez on Milton Ritzenberg’s Explosive Madam at Pimlico in 1991 to Emily riding Frost a Lot at Piedmont Point-to-Point in 1996 to Spy in the Sky’s A.P. Smithwick in 2012.

They’ve been able to cultivate loyal clients, who play the game for the right reasons. Virginians Edie and Bruce Smart have had horses–never a bunch, but always a few–with the Days for nearly two decades.

“Jimmy has become one of my very best friends, we not only share a love of horses, but we also are compatible as people. He’s the most optimistic person in the world, I remember a point-to-point, he had four horses and each one finished second, he said, ‘Don’t worry about it, no one is going to beat any of them again this year,’??” Smart said. “You have to have a harmony between rider and horse and you have to harmony with people on two sides of a business deal, and in due course, it often develops into a friendship. We’ve had a lovely time.”

Typically, the Smarts campaign a home­bred or two and a purchase or two, sometimes in partnership with Daybreak. Presently, they own all or part of six horses at Daybreak. Last year, Bonded, secured for 11,000 guineas by Day at Tattersalls in 2010, won an allowance race at Saratoga and a flat race at Great Meadow. Encapsulating the Days’ type of client, you couldn’t tell the difference in the race by the reaction from the owners.

Sportsmen.

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Just as Mandy’s Gold and Like a Bull helped build specific things on the farm, Diplomat did his share last year. Purchased for 11,000 guineas (must be Jimmy’s sweet spot) from Dermot Weld’s draft at Tattersalls in October 2014, Diplomat ran for the house, winning the Carolina Cup, picking up three minor checks and winning an optional claimer at Saratoga. Claimed from his Saratoga win, Diplomat grossed $135,000 in 10 months. That’s lucrative on anybody’s docket, but in the Days’ model of owning a few themselves, training for small owners, on a working farm, doing most of the work, it’s a game changer. Bittersweet, slightly. Pragmatic, absolutely.

“In Ireland, before I came over, I said I would never train, but when I came over and worked for Burling, I thought this mightn’t not be a bad business to be in,” Jimmy said. “I always wanted to breed. But it costs so much to breed. We did the breeze-ups, well-bred fillies, if they didn’t work, we were in the business.”

Emily finished the thought.

“That’s been the saving grace, we’ve got so many options, because Jimmy trains on the flat, he trains over jumps, he trains on the dirt, he trains on the turf,” Emily said. “And I like to do the showing and fox hunting, so there’s always a lot of avenues for the horses who come here.”

Jimmy continued.

“You’ve got to do other things, I make my own hay, I know what the horses are eating, that saves me money, it’s a lot of work, I sell round bales, I enjoy it, I’m out on the land.”

Asked if he’d changed anything, Jimmy didn’t hesitate.

“I’m in the process of trying to change right now, wean away from day-to-day training and get more into the sales, not in a big way, but I would like to have at least two breeze-ups every year, maybe we have to start buying weanlings,” Jimmy said. “I do enjoy the jumpers, I enjoy training on the farm, I get a lot of satisfaction of training them, I don’t go racing much, I can’t do a whole lot once they get on the truck and there’s nobody back here to work next week’s runners.”

At the end of the February afternoon, the rain had stopped, Emily and Jimmy stood outside their house and thought about life.

“We’re doing pretty well, we get discouraged every once in awhile but we say, ‘Look at what we’ve been able to do so far,’?” Emily said. “Getting two kids through college. . . that’s our greatest accomplishment.”

Jimmy nodded, there was no disagreeing or correcting now.

“That takes a lot of pressure off,” Jimmy said. “There’s always going to be pressure, but getting them through college, that was the main thing.”

Two college graduates. A room full of win pictures. A barn full of good horses. A bucolic farm. One strong marriage.

Five lines of achievement, none happen without the other.

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